


A Change In Plans

by BSBLover2538



Series: BSB AU Fics [1]
Category: Backstreet Boys
Genre: Come Swallowing, Dominance, F/M, Hand Jobs, Master/Slave, Mental Breakdown, Mind Manipulation, Service Submission, Snark, Submission
Language: English
Status: Completed
Published: 2019-08-28
Updated: 2019-08-28
Packaged: 2020-09-28 12:28:49
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 7,177
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20425988
Author URL: https://archiveofourown.org/users/BSBLover2538/pseuds/BSBLover2538
Summary: During the hiatus in 2003, Kevin starts performing on Chicago. He meets an interesting stagehand, and over the years, gets caught in her web until she has him right where she wants him.





	A Change In Plans

Kevin grinned as he went into the theater for another day of rehearsals for  _ Chicago _ , hoping to see the snarky stagehand that worked for the theater. It had been a couple of weeks since he had joined the company, and had quickly taken a liking to the young woman. As he made his way to his dressing room, and his eyes lit up seeing her pass him. 

“Hey Jillian” he smiled and chuckled to himself as she rolled her eyes, passing him on her way to go do something. 

“Stupid pop star wanting to crash into our Broadway show” she muttered to herself as Jillian went to find the stage manager, having noticed something slightly off with the lighting in the second act last night. 

She sighed as the actors all made their way to the stage, the director calling out a scene he wanted them to rehearse. Jillian stood off to the side, keeping a keen eye on the lighting in the act, this being the scene where it was off. The grating voice startled her out of her concentration. 

“How was your night last night?” Kevin asked, as he watched the scene being played out. He wasn’t in it, so he had time. The older man looked over at the shorter girl next to him, a wide smile on his face. 

“Shut up and leave me alone Richardson” Jillian growled, as she focused back on her job. Kevin didn’t take her advice, and started talking inanely about his night with his wife, not that Jillian gave two  shits . 

“Richardson, if you don’t want to sing at a higher range tonight, I advise you to remove yourself from my firing range” Jillian looked up and scowled, her blue eyes on fire. 

“Okay, okay, just trying to make conversations jeez” Kevin put his hands up in peace, and walked away. Jillian sighed happily as she focused back on her job. 

Over the next couple of weeks, Jillian tried to keep up the snarky facade around Kevin, but soon found herself taking longing glances at the older man. She knew he was married, but Jillian had a few tricks up her sleeve. She was an expert at getting men under her, and used her looks and  snarkiness to get them to fall for her, before she trapped them. 

“Richardson, you aren’t half bad anymore” Jillian looked up at the older man, smiling softly, a hint of  snarkiness in her tone. 

“Does that mean I get to hear my first name come from you?” Kevin asked, and Jillian smirked. 

“Maybe, but only if you continue to stay on my good side. Can you grab me a coffee, black?” she asked, and Kevin nodded. He darted off to the coffee shop nearby, and delivered the coffee to her in under 10 minutes. 

“Thanks, I appreciate that” Jillian smiled to herself seeing Kevin get a little red at the praise. She knew she had to take it slowly, and that’s exactly what she did. A coffee here, a small sandwich for lunch there. Soon, Kevin was spending the time he didn’t have to be on stage or at home with Kristin with Jillian. 

“Kevin” she said one day, and the older man looked up at her in surprise. This was the first time she had ever said his first name. It sounded like honey coming from her lips. 

“Yes Jillian?” he looked at her, ready to do whatever she said or asked. 

“Can you grab me a few things? If you get back in under an hour, I’ll have a present for you” Jillian smiled as Kevin nodded eagerly. 

“Of course, what do you need?” Kevin listened as she gave him her list, and darted right out of the room after she dismissed him. 

Jillian smirked to herself, and knew that her plan was going smoothly. She just had to wait for something bigger to happen to make Kevin fall a little deeper. Jillian had been doing this for years, and knew to take it slowly. 

Two days later, and Jillian’s cell phone rang. She smiled to herself as she answered the phone call. The voice on the other end had her laughing to herself. 

“Jillian, thank god. Can I possibly come over? Kris and I got in a fight, and she kicked me out for the night. I don’t want to go back to my bandmates right now, and I’ve got nowhere else to go” Kevin asked. 

“ Sure come over, I have a pull out bed you can use” Jillian gave him her address, and smiled to herself as she hung up. Time to start the set up for the next part of the plan. She knew exactly how to handle this. Ten minutes later, she opened her door, and looked tenderly at the broken man in front of her. 

“Come here Kevin, let’s sit and relax” Jillian took his hand, and led him to the couch, sitting him down, and going to get some refreshments, while locking the door just to be safe. It was New York after all. 

“What happened?” she asked, as she rubbed his back gently. 

“Kris got upset with my late nights, and she accused me of cheating on her. I tried to tell her that I wasn’t but she wasn’t listening. We got into an argument, and she threw me out for the night” Kevin explained, and Jillian nodded her head softly. 

“I’m so sorry to hear that Kev, anyone who knows you, knows you wouldn’t cheat on your wife. Has this happened before?” Jillian asked, continuing to rub his back. 

“We have had some disagreements, especially when the group took its hiatus. After realizing that I would be around more, the arguments came quicker and easier. I married her for better or worse, but this is getting tiring” Kevin rubbed his eyes, and wiped the tears. 

Jillian just continued listening and talking to Kevin, her hand never leaving his back. She reassured him that he was still an amazing husband for his wife, and apologized to him for all the  snarkiness she had thrown his way. Kevin chuckled softly. 

“That’s often the best part of my day. Love spending time with you, and I know you have a hard time at the theater” Kevin smiled down at the younger woman. 

“I still am  sorry, I just get into the mindset with my job. I hate getting thrown off my schedule, and I finally realized that you were just being nice and friendly” Jillian looked up at Kevin, and the older man just hugged her before letting her go. Jillian set him up on her pull out couch, and went to her own room. 

“He trusts me, thinks I really do care about him and his marriage. I’m getting there. Just need to bide my time some more. This is working out well, just have to be careful” Jillian thought to herself as she fell asleep, beyond ready to get Kevin under her completely. 

Over the next couple of months, Kevin continued performing until his run ended. Jillian had tried to get him under her some more, but only succeeded in a few more ways, but not completely. When Kevin announced he was leaving, Jillian was heartbroken. She really thought she would get him completely under her, but it seemed it was not to be. 

“All that work, down the drain” Jillian sighed softly, sitting in her apartment. She had forgotten that Broadway runs sometimes weren’t all that long, and she should have expected this. Jillian shook her head, and pushed the thoughts of Kevin kneeling next to her, laying his head on her lap as they watched TV out of her head. 

“I need to stop with the actors, this always seems to happen” Jillian threw herself back into work, forgetting about Kevin, and not trying to seduce anyone else. She had fallen for the older man, and no one could measure up in her eyes. She focused on work, and just lived her life, part of her heart always hoping that Kevin would come back around. 

Across the country, Kevin had settled back down with Kristin, but things weren’t going well. The fights and arguments were constant, and Kevin wasn’t happy at all. His mind kept drifting back to doing Broadway again, just to get away from his marriage for a bit. Things with his vocal group were completely silent, and he barely spoke to any of them. Jillian kept entering his thoughts as well, and Kevin wasn’t sure how much longer he could take it. 

“When are you going to go do something?” Kristin walked in, and crossed her arms, glaring at her husband. 

“I have been  Kris, I’ve been working again on Chicago out here in LA. You wanted me closer to home, so I came home. What more do you want?” Kevin looked at his wife, sighing softly. 

“Just stay out of my way. I wish you were back with that damn group, so you weren’t home so damn often” Kristin stalked away, and Kevin rubbed his temples, trying to soothe his headache. 

“Damn I miss Jillian and her  snarkiness . I felt so calm, and like I could be me around her” Kevin thought as he settled down for the night. Kristin had slept in another room, and Kevin was getting tired of her behavior. It had been nearly six months, and nothing had changed. 

Things for both Jillian and Kevin didn’t change for over two years. One in LA, in a horrible marriage, the other in NYC, working like a dog, trying to forget about the man who had left a lifelong impression on her. The two missed and pined for each other, but knew that they weren’t likely to see each other again. Jillian didn’t know where Kevin lived, so when she planned to move out to LA after an amazing job offer, she didn’t realize she would be closer than ever to seeing him again after almost three years apart. 

“Hey we have someone new coming in as Billy Flynn today” the stage manager announced, and Jillian rolled her eyes. She hated when new people came in, and resolved to up her  snarkiness and cold behavior once again. As she was talking to her coworker, she heard a voice that she hadn’t heard in so long. 

“Jillian…” Kevin called out, and saw the brown hair of the woman he had missed for so long, whirling around. He smiled as she ran towards him, giving him a hug. 

“Three years, no contact, and now you show up?” Jillian asked incredulously, and internally smirked as Kevin blushed softly, ducking his head. 

“Sorry Jillian, I ended up back with the guys, and recorded an album, touring it. I decided to step away for a while, and decided to act again” Kevin explained. 

“While I stayed in NYC for a while, and just moved here to LA a few months ago. I got an amazing home, and am finally getting myself settled around here. Why don’t I show you where your dressing room is?” Jillian offered, and Kevin nodded instantly. 

“Yes please”  Jillan smiled and Kevin followed her to his private dressing room he had. He got himself settled down, and Jillian left to get something done, before coming back. 

“ So what’s been going on? Still married?” Jillian asked as she plopped down on the couch in Kevin’s dressing room. 

“ Yes I am, and its same as it’s always been. Thank god we don’t have kids. It got slightly easier when I got back on tour, but now that I’m home again, its three years ago all over  again. I needed to get away” Kevin sighed, as he looked at Jillian. 

Jillian smiled to herself, and continued talking to Kevin, catching up. She couldn’t believe her luck. Maybe now she could finally ensnare him completely, and get him right where she wanted him. The fact that he had already slightly submitted to her again, made things that much easier for her. 

The two worked together again, and things fell right back into place with Kevin grabbing things that Jillian needed. Once they were back in that routine again, Jillian knew she could start making moves on Kevin, letting her dominance show through a bit. 

“Hey Kevin, how’s it going?” Jillian asked as she trailed her fingers up his arm, squeezing his shoulder a bit. Kevin nearly buckled under the squeeze. He shook his head and looked down at the younger woman. 

“It’s going well. You will be happy to know I extended my contract. I’ll be around for another year and a half” Kevin grinned softly as Jillian looked at him in disbelief. 

“Really?” she asked, and Kevin nodded eagerly. 

“That’s amazing. So happy to hear you are staying around” Jillian couldn’t believe her luck. She knew by the end of his contract that Kristin would be gone, and he would be ready to fall for her. Jillian smirked lightly to herself, but focused back on Kevin. 

“ So when are you going to tell Kristin?” she asked curiously, and Kevin paled a bit. He knew she was pushing him to go back to his vocal group. 

“Soon. My original run doesn’t end for another month. She will have to get used to it” Kevin said resolutely, but Jillian could hear the hesitation in his tone. She brushed it off, and changed the topic. 

The next couple of months passed the same way, with Jillian occasionally touching Kevin, rubbing his arm, or trailing her fingers down his back as she hugged him. She could always tell he was affected by it, seeming to melt into her touch. Kevin also started spending more time over at her place, late into the night. They would talk about anything and everything, and Jillian knew that he was avoiding Kristin. 

“What happened when you told her you were sticking with acting?” Jillian asked one night as she kept an arm around him while they watched TV. 

“She wasn’t happy in the least. Kristin decided that my punishment was no sex, so I’ve been using my hand for the last two months. She won’t touch me, barely even speaks to me” Kevin sighed, dropping his head to his chest. 

“And you still want to remain married to her, why?” Jillian couldn’t understand why Kevin was staying in his marriage. 

“My marriage vows mean something to me. I think she is cheating on me though. I can’t get proof though” Kevin sighed, and played with his fingers. He pushed down his erection, which had started flaring whenever he was around Jillian. 

“You can take care of that, I don’t care” Jillian smiled, and looked at Kevin, before palming his erection through his jeans. Kevin’s eyes widened, and he moaned loudly. 

“Shit!” it had been months since another woman had touched him down there, and his whole body reacted. 

Jillian smirked and dragged her hand down his erection, before squeezing the tip. Kevin nearly arched into her touch, panting softly. Jillian took her hand away, and looked at Kevin. 

“Might  wanna do something about that Kevin, looks pretty painful” Jillian grinned, and Kevin glared at her. 

“No thanks to your “help”. Thank you so very much for that” Kevin groaned as he undid his pants, pulling them down. 

“Want me to help?” Jillian offered, and Kevin whined softly, as she put her hand down his boxers, grazing his cock. Kevin nearly came just at her small touch. 

“Please” Kevin whimpered out, and Jillian wrapped her hand around his cock, stroking it gently. Kevin cried out, knowing he wouldn’t last long. A few strokes later, and he was  cumming all over  Jillian’s hand. 

“Need to hold back better next time” Jillian muttered to herself, realizing that she would need to train Kevin to hold his orgasms back until she commanded. Kevin was too busy panting, coming down from his high, to hear her. 

Kevin put his cock away after coming down from his high, and Jillian went to clean up her hand. Maybe next time she would order him to clean her up. They settled back down, before Kevin had to leave again. 

As Kevin drove home, his thoughts were consumed with what had happened a couple hours before. He could still feel Jillian’s hand around his cock, stroking him off. It had been months since anyone had touched him, and he wanted it again. His hand didn’t feel right anymore. Kevin’s eyes widened as he came to a realization. 

“Jillian’s hand felt like it was meant to be around my cock, like that is what was missing. I have never felt like that with Kristin, her touch felt all wrong” Kevin thought and he pondered the implications of that statement. 

Kevin tried to keep the look of bliss and happiness off his face when he entered his home. Luckily Kristin was already asleep in the guest bedroom, so Kevin walked into the master, and stripped his clothes off, looking at his cock. He wanted Jillian’s hand back around it, desperately. 

“Fuck, I need her touch again” Kevin thought as he tried to fall asleep. It proved difficult, and Kevin laid awake, thinking about Jillian, Kristin, his marriage, just everything. Kevin wondered what would happen in the future, but he couldn’t worry about that now. He fell asleep to images of Jillian’s hand back on his cock, stroking him, and running her hands down his naked body. 

The next couple of weeks proved to be torture for Kevin. Things had become busy with the show, and Jillian couldn’t spend much time with him after work. She would get up, go to work, and come home and pass out. Kevin hadn’t touched himself at all, and was about to go spare with need. He wanted her touch back on him, and wanted to wait until she had the time. 

“You free tonight Kev?” Jillian asked, and Kevin nearly screamed an affirmative. Jillian internally smirked, and knew that she was inching closer to her ultimate goal. The major roadblock was Kristin, and Jillian knew that something drastic needed to happen. Jillian  coverly got her plan together, and smirked to herself. 

“Come on Kev, let’s walk back to my place, it’s a cool night” Jillian suggested, and the older man nodded. The two linked arms, as they were  want to do, knowing that Kevin’s place was in the opposite direction. Jillian talked about the recent struggles her department had been having, griping about an unhelpful coworker, and Kevin listening attentively. The two were close to Jillian’s apartment building, and neither noticed the cameras going off in the distance, getting perfect pictures of the two of them looking cozy together. 

“ Finally home. Sit down and get settled, I’ll be right back” Jillian went to change, and Kevin sat on the couch, adjusting his jeans so his cock wasn’t crushed. 

“Again, really Kev?” Jillian asked as she walked back in the room, noticing the tent right away. 

“I haven’t touched myself since you touched my cock last. It’s been painful. I need your touch again” Kevin nearly whined petulantly. Jillian raised an eyebrow. 

“Kevin ….. what’s with the attitude? I don’t have to help you, you know that. You can use your hand” Jillian reminded the older man. Kevin’s face flushed and he lowered his head. 

“Sorry Jillian, I apologize. May you please touch me again?” Kevin looked up hopefully, and Jillian sat next to him, taking his cock out again. 

“Wonder if you will last longer this time” she mused, as she stroked his cock. Kevin heard her words and turned red. He knew that he had cum quickly the last time. He screwed his face up, and promised to himself to last longer today. 

“There we go, love feeling the throbbing in my hand” Jillian grinned as she continued stroking him, jerking his cock a bit, feeling it get thick in her hand. Kevin nearly arched into her touch and panted, trying to hold his orgasm back. 

“Fuck” Kevin whimpered out, as he fisted the couch cushions, trying to hold on. It had been nearly ten minutes of torture, and his control was barely there. Jillian looked up, and after a firm tug, she watched him let go, calling out her name. 

‘Good boy” she praised, and saw Kevin blush hearing her words. She smiled and took her hand off his cock, holding up her soiled hand. 

“Ever want to try  your cum Kevin?” she asked curiously, and he looked at her, then her hand, and back again. He bit his lip, and nodded his head. 

“Go ahead, lick it, try it out” Jillian encouraged, and Kevin licked a stripe off her hand, tasting himself for the first time. His eyes widened, and he went back for a second lick, loving it. Jillian grinned watching him clean her hand, and she knew that things were falling into place. 

The two cleaned themselves up, and snuggled again, before Kevin left for home. Jillian knew she would be getting a call around 8am the next morning from Kevin. 

“KEVIN SCOTT RICHARDSON!” Kristin’s voice screeched as she slammed open the bedroom door, startling Kevin awake. 

“What’s going on?” he asked, trying to wake up. A magazine was thrown at his head, and he looked down, staring in horror at the photo of him and Jillian walking near her apartment. His hand had wrapped around her back, and he was leaning down towards her, to hear her better. 

“This! What is the meaning of this? Who’s the girl Kevin, another skank?” Kristin asked venomously, and Kevin rapidly shook his head, getting out of bed, and going to his knees. 

“Kristin, I promise nothing happened. She’s a friend from the show, and she needed some help last night. She means nothing to me at all, please believe me” Kevin explained, as Kristin looked at him disgusted. 

“You  cheated didn’t you? This is the second time! I never should have married your ass all those years ago. I knew you couldn’t keep it in your pants. This is fucking pathetic. I’m done Kevin, this is the end” Kristin looked at her soon to be ex with hurt and hatred in her eyes. 

“Please Kristin, I promise that nothing happened. I didn’t cheat” Kevin pled, but Kristin shook her head. 

“You came home smelling of another woman last night. I smelt perfume that wasn’t mine, and you looked too entirely happy for just helping someone. I’m done! I’ll be out of the house by the end of the day. Thank god we don’t have kids, or this would be even more pathetic” Kristin slapped Kevin across the face before leaving. 

Kevin’s face crumpled as he felt the sting of the slap on his cheek. He bent his head and curled into a ball, crying. He waited until he heard the car leave, before scrambling for his phone. Kevin dialed one number, and waited for her to pick up. 

“Jillian, I need you. She left me, apparently someone got pictures of us together last night, and it was in a magazine this morning” Kevin got out, and Jillian gasped softly, playing the role of a caring friend to the hilt. 

“Oh my god Kevin, I’m so sorry! You can come over, or I can come to you, whatever you want. I will ask my neighbors, see if they saw anything” Jillian spoke caringly, and Kevin hiccupped. 

“Thanks Jillian. I’ll text you my address. Can you tell the stage manager that my understudy needs to go on tonight? I can’t tonight. Thank god it’s Monday tomorrow” Kevin knew he was in no condition to do the play tonight. 

“ Yes I will. I’ll be there soon I promise” Jillian hung up and smirked to herself. The plan went off without a hitch. After some loving and caring, Kevin would be in her web enough to fall. She just needed to bide her time until he realized what she was doing, and realize that he needed her in more ways than he thought. 

Jillian made her way over to Kevin’s, and looked at the nearly broken man in front of her. She knew that getting in while he was vulnerable would be the best way to get more control over him. Jillian got him off the floor and into her arms. 

“Want to come back to my place?” she asked, rubbing his back. Kevin looked down at her and nodded softly. 

Kevin leaned into her touch, loving the feeling of her hands on him. The two packed a bag for Kevin, and he made his way over to Jillian’s the younger woman going ahead of him. As he got into her home, he cried again. Jillian pulled him into her arms, holding him close, letting him cry, rubbing his arms and back. 

The next couple of days were spent getting Kevin used to her touch, and Jillian helped him through everything. She started giving him simple things to do, to take his mind off the entire situation, and she took care of his cock a couple times. He wanted her hands on him at all times, feeling like they were meant to be there. 

“Kev, what happened?” Jillian had gone out to get groceries, and came home to Kevin crying again. One look at her coffee table, and she knew what he was upset about. 

“What are you going to do?” she asked, and Kevin looked at her with bloodshot eyes. 

“I’m not going to fight it. I just want it over with. I’m going to sign them, and just let it go” Kevin sighed and Jillian nodded. 

“Okay, if that is what you feel is best. What’s going to happen now?” she asked curiously, and Kevin groaned. 

“I don’t know. I’m going to give her the house. I have to figure out where to go” Kevin flopped back on the couch, and Jillian pounced. 

“You can stay here. I have an extra bedroom. Just move your stuff in there” Jillian offered, and Kevin immediately accepted. A day later, the two were settled in, living together as roommates, but Jillian knew it wouldn’t take too much longer. 

Kevin had about three months left on his contract, and had told Jillian he wasn’t going to renew it. Jillian asked what he intended to do afterwards, but Kevin wasn’t sure. He was slowly getting used to what Jillian had been doing, and found himself automatically obeying her when they were at home together. 

“Jillian, can I ask you something please?” Kevin asked one night, and Jillian turned towards him and nodded. It had been a week since his contract had expired, and Kevin got notification that his divorce had gone through. He was single again, and very happy about it. 

“ Of course Kevin, what’s going on?” Jillian had no idea what he could be asking her. 

“What is going on between us? Why am I so willing to do what you say, and why am I craving your touch and words so much?” Kevin asked, and Jillian’s eyes widened. 

“Fuck, he caught on. Shit, how do I explain this” Jillian’s mind raced, before she came up with something. 

Jillian sat down next to him, and put a hand on his arm, rubbing it gently. Kevin felt his body relax under her touch, and looked at her. 

“Why are you feeling like that Kev?” she asked, and Kevin shook his head, trying to clear the fog that always came when she touched him. 

“It just feels really good. I feel like I need your touch all the time, like its right to have you touching me all over my body” Kevin explained, and Jillian smiled softly. Now was the time to set the bait, see if he took it. 

“Do you want to feel like that all the time? Get my touches, and feel my fingers on your body, feel so good when I praise you? Do you like following my orders Kevin?” Jillian smiled, never taking her hand off his arm, trailing her fingers down it gently, looking at him. 

“Yes, yes I do” Kevin whimpered out, the hazy feeling coming back, wanting more and more of it. Jillian grinned and kept up her movements, watching him fall further and further down. She pulled her hand away, knowing he couldn’t completely fall yet. They had a few more discussions to make before she could have him completely fall and submit wholly to her. 

“Jillian….” Kevin whined out as he came up from the haze. He wanted to feel it again, he loved feeling that way. 

“We need to talk before you can fall Kevin. Tell me when you are feeling normal again”  Jilian got up and started making food for them. Kevin thought for a long time, and realized that the way Jillian made him feel, was exactly what he needed. He needed what she gave him. Kevin got up, and went to go help Jillian out with making the food. He eventually scooted her out, and finished it up himself. After the meal, Kevin took Jillian’s hand, and they went to the couch again. 

“You ready to talk?” Jillian asked, and Kevin nodded. He was as clear headed as he had always been, and knew that this discussion was important. 

“First of all, if you want to fall, we need to discuss your limits, and hard no’s. I will be having you sign a contract, covering my butt and yours. It will have a clause saying that you can opt out at any time, but something tells me you won’t be doing that. Do you want to know exactly what would be happening, and what your life would be?” Jillian looked seriously at Kevin, who nodded. 

“You would be broken completely by me, and I would control everything about you. You would not be able to go back to the group, nor leave the house. You would have no contact with the outside world in any way. You will be my slave and sex slave. All chores will be done by you, and you will be ready and willing to be fucked, or take care of me, anytime I ask. You will have chores and punishments. All of your possessions would become mine, even your name. I will only refer to you as whore, slut, or slave, depending on my mood. I control everything” Jillian looked at Kevin, showing the most amount of dominance she had ever shown him. 

Kevin gulped, and lowered his head right down as he thought. The thought of being nothing more than a slave for Jillian was all he could think about. He wanted that, he wanted to be hers. He looked up at the squeeze she gave his hand. 

“And Kevin, any and all good behavior will be rewarded. I will not have you live in fear that I will only look for the things you do wrong. I am not like that. I will notice and praise your good behavior, but you have to earn it. Understand?” Jillian looked at the older man, who nodded his head. 

“Yes Jillian, I understand” he lowered his head back down and thought some more. The idea of leaving his brothers behind and the whole world as well hurt, but not as much as he thought it would. He sat in the quiet for a good fifteen minutes, Jillian giving him all the time he needed, staying quiet. 

“I’ll do it. I will fall. I want  this, I want what you give me” Kevin looked up at  Jillian, who only nodded her head. 

“Stay here, and I will get a pen and paper. We need to have more discussions” Kevin inclined his head, and Jillian got up, disappearing into the bedroom. 

Over the next two hours, the two of them wrote up a contract, and Kevin listed his limits and hard No’s. Jillian made three copies of that list, and told him one would be going in the bedroom, so that Kevin knew his limits were being respected. The older man nodded his head, and Jillian looked over the contract, having experience with writing a Dom/Sub contract. She handed it to Kevin, with a pen. The older man took his time looking it over. 

“This is it. I sign this, I basically sign my life away. Do I really want this?” Kevin closed his eyes and thought. A few minutes later, he opened them, and looked at the contract, before looking at Jillian. He took a deep breath, and signed his name to the contract. As he put down the pen, he blew out the breath, and an overwhelming calm came to him. He had done the right thing, and he knew it. Jillian just smiled, knowing that her plan was almost complete. 

The younger woman looked at her new submissive, and knew that she couldn’t take him that night. During their discussion, Kevin had asked for one day, to go see his brothers, and say goodbye to them. Jillian had granted it, knowing that him suddenly disappearing would cause more problems than it was worth. She wanted him under, but knew that things had to be squared away first. 

“Thank you for this Jillian” Kevin said the next morning as he left to go see his brothers for the last time. Jillian just inclined her head, and kissed his cheek. She smiled seeing the red bloom, and watched him leave. This actually gave her time to prepare the home for him. She got everything ready, and knew that once he walked in the door, it would be the last time, for he was never leaving the home again. 

Six hours later, Kevin walked in the door, and he knew it would be for the last time. He had said goodbye to his brothers. The explanation had been difficult, but he gave vague details, and they understood. Luckily Howie’s brother and Nick’s sister had done the same thing, so the guys roughly knew what Kevin was talking about. They shared a heartfelt goodbye, and Kevin knew he would never see them again, and he was completely fine with it. 

“You ready My submissive?” Jillian asked as Kevin got his shoes off, giving him a hug and kiss. Kevin took a deep breath and nodded. 

“ Yes I am, I am ready to fall Jillian” Kevin replied, and Jillian sharply nodded. She took him in her arms, and started trailing her fingers down his body, taking his clothes off slowly. Jillian watched as Kevin’s eyes started falling, the haze beginning to take over again. The older man whimpered softly as she took her hands off of him. 

“Bedroom now” she ordered, and Kevin hastened to obey. She followed him, as he wondered what to do now. 

“I tell you where to go, then you go to your knees and wait. That will happen automatically after you are broken. Understand?” Kevin looked at her and nodded, falling to his knees. Jillian took a moment to circle him, marveling at the view of Kevin on his knees for the first time. She couldn’t believe that the plan she had started making four years ago, was finally coming to fruition. Jillian had her submissive, her slave. 

“On the bed, all fours now!” Kevin scrambled to obey, and Jillian went to get her strap on around her. She smiled seeing him looking ready and willing to be fucked. 

“You know what is happening right Kevin?” she asked for the last time, and Kevin nodded his head. 

“ Yes I do Jillian, completely” Kevin nodded, and Jillian ran her hands down his body. She ran her fingers down his ass, feeling the puckered skin around his hole. Jillian considered her options, and decided on what to do. She went around to face him. 

“Kevin, since this session is breaking you,  My toy will be lubed, but your hole will not be. I promise this is the only time you will be taken like this. Any other time, you and the dildo will be lubed. The pain you will experience will help with the breaking, and will help you slip further into the haze you are experiencing. Do you understand?” Jillian gave her submissive a serious look, and watched as Kevin thought about her words, and he nodded. 

“ Yes Jillian I do understand. I knew you would not hurt me intentionally, and I did tell you that pain is one of my kinks. Thank you for the warning and reassurance. It does help” Kevin smiled at her, and Jillian nodded, kissing his forehead. She went back around to his ass, and grabbed the lube, covering her dildo. She widened his hole as much as she could without lube, and took her fingers out. 

“It is happening now Kevin” was all she said. Kevin nodded, and then screamed as she pushed into his  unlubed hole. Jillian pushed all the way in, before pulling out, and slamming back in. Jillian could see in his body language that Kevin was falling, and the hazy, submissive feeling was taking completely over. 

“What are you Kevin?” she asked, grunting softly. 

“A slave, something for you to use and play with” Kevin replied, his voice hoarse from screaming from the pain. 

“Who owns you?” Jillian looked down at her slave, still pushing in and out of his hole. 

“You do, Mistress owns slave” Kevin cried out and Jillian nodded. 

“ Yes you are and yes I do. You are My slave, My whore, My slut. Mistress is so proud of her slave” Jillian accentuated each statement with a thrust in. She did it a final time before pulling out. Kevin collapsed on the bed, before getting up on shaky limbs, knowing to go to the floor and kneel. 

“Good slave” Jillian praised Kevin, before going to her dresser, getting his collar. She walked back over, and slipped it around his neck, tightening it. Kevin looked up at her with bright green eyes, the haze having completely over. 

“How do you feel My slave?” Jillian asked, and Kevin licked his lips. 

“Slave feels good Mistress, feels like  slave is right where he is supposed to be” Kevin replied, and Jillian ran her hand through his hair. 

“Good boy. Mistress is proud. One last thing My slave. Can’t have you getting off when you aren’t allowed to” Jillian went back to her dresser, grabbing the cock cage. She slipped it onto Kevin’s cock, he just watched her do it passively, not fighting it at all. 

Jillian stood back and admired the view of her slave. Kevin was kneeling, cock cage and collar on, head down, and just waiting for her to command him. She sat down at the edge of the bed. 

“Slave here now” she ordered, and Kevin crawled over. She grabbed his hair, forcing him on the dildo. Jillian groaned watching him suck eagerly on the toy, knowing that the next month or so would be spent training him completely. In about two  months time , she would have the perfect obedient slave for her. 

Six months later, Kevin was settled completely into his life as a slave/sex slave. He had a set routine he followed each day, and obeyed Jillian faithfully. He was praised for his good behavior, and punished if he misbehaved. After about a month, he no longer thought about the outside world, and being in a singing group was a distant memory. All Kevin thought about was serving his Mistress, and being a good slave for Her. The only thing he wore was his collar and cock cage. Jillian let him off the cage every 10-14 days, before snapping it back on. Kevin had been trained to orgasm at Jillian’s command, and knew every one of her commands for him. 

“Slave, come to the bedroom” Jillian called, and Kevin scurried there, kneeling right down at her feet, head down. 

“Eat me out” Kevin nodded, following Her order. He expertly ate his Mistress out, cleaning her completely. 

‘Good boy. Go make dinner, and then go to your spot” Jillian looked down, and he nodded. 

“Yes Mistress, slave will let You know when supper is done” Kevin waited for Her to dismiss him, and he went right to the kitchen. 

“Mistress, supper is done” Kevin called, before falling to his spot next to Her seat. Jillian made her plate and his bowl, setting it down on the floor for him. She ate her dinner, speaking to Kevin about different things, and Kevin laid her head on his lap once he was done eating. 

“ Tonight My slave gets a treat” Jillian told Kevin to go to the bedroom, and spread. The older man nodded, doing exactly as she stated. Jillian walked in, and right to him. She took the cock cage off, and started stroking his cock, much like she did when Kevin had first started to fall. 

“My slave, so proud of him. He is perfect for Me, and so obedient. Do you remember doing this slave, before you fell?” Jillian asked, and Kevin thought. Most memories before falling were hazy, and her touching him like this only added to the haze. 

“No Mistress, slave is sorry, but he doesn’t remember. Slave is ready to accept punishment if You deem it so” Kevin replied, and Jillian shook her head. 

“You will not be getting punishment My  slave, you answered the question honestly. That is what Mistress wants” Jillian continued stroking Kevin’s cock, knowing he wouldn’t let go until she commanded. 

“Cum whore” Jillian ordered, and Kevin cried out as he let go all over Jillian’s hand. She didn’t stop until he was completely milked. Jillian lifted her hand up, and Kevin cleaned her hand, tasting himself once again.  Jillian led them to the shower, cleaning her whore up, before putting the cage back on. 

“It is time for bed My slave” Kevin nodded, and went to bed, laying on his side. Jillian grabbed her strap on, and slid right into his hole, knowing Kevin was permanently loose from how much she fucked him. 

“Mistress loves you My slave” Jillian wrapped her arms around Kevin, feeling him settle down. 

“Slave loves his Mistress” Kevin replied sleepily, and he fell asleep in his loving Mistress’s arms, ready for another day of serving Her tomorrow. 

Jillian grinned and tightened her hold on her slave, and wondered what was going through Kevin’s head. Said man was thinking about how different his life was, and meeting one girl led to a change in plans for his life and he couldn’t be happier that he had pursued his Mistress like he had. It has led to an amazing life for him, and Kevin was never happier or more content than he was serving his Mistress, and being available to Her. Kevin would never change his life for anything, and he was grateful to Jillian for everything she had given him, and would continue to give him as the years went by. 


End file.
